Cassie
Copyright© 2025 by TheDarkKnight
Chapter 4: Cassie Becomes a Woman
Fiction Sex Story: Chapter 4: Cassie Becomes a Woman - I come from a family of teachers and educators, so becoming a teacher was what everyone expected of me as I was growing up. However, after I earned my degree and started teaching, I found that being around teens and tweens only fueled my formerly hidden perverse interests. I thought that taking a job as an online tutor might be the answer, then I met my new neighbor, Cassie. Frying pan, meet the fire.
Caution: This Fiction Sex Story contains strong sexual content, including Ma/ft Romantic Heterosexual Fiction First Oral Sex Petting Small Breasts Teacher/Student Slow
Fear is a great motivator, but so is lust, and I was feeling both emotions as I headed into a weekend alone with Cassie. I debated, wondering if letting her sleep with me and give me a hand job was really that much less of a sin, or against the law, than taking her virginity would be. I knew the answer, but it didn’t stop me anyway.
Since there was no school on Friday, due to the storms, I thought it would be a good time to use it for a cooling-off period. I know I needed it. I suggested going to a new mall in a part of town that had escaped serious damage. Cassie was all for it; what teenage girl wouldn’t be?
As soon as I suggested it, she asked if Sally could come with us. “Sure,” I told her, “as long as her parents don’t mind.”
That only took one quick phone call, then Cassie told me, “Her parents are okay with it. They trust you.” She couldn’t keep a straight face when she said that and broke out in a string of giggles.
An hour later, we walked into the Golden World Mall, a very pretentious name, and an indicator that I probably wasn’t going to be buying much there. It was busier than I had expected, maybe because it was new and school had been canceled for half the county. It seemed like it was full of teenage girls, but perhaps that’s because I tend to notice them more than the old mall-walkers and families with toddlers. One thing I noticed right away is that those nymphets were roaming the mall in groups of two, three, or even once five, and hardly any of them were escorted by an adult. I quickly got the idea and told Cassie and Sally I would meet them in the food court for lunch later, and left them alone.
To kill some time, I checked out the Apple store for devices I would probably never buy, being more of an Android guy. I checked out a couple of shoe stores, then saved the best for last - the bookstore. I started browsing, then decided that since I was there, I might as well buy something. I bought a book about horses - caring, training, riding them - for Cassie. I found a book on chess openings for Sally, and two books of New York Times crosswords for myself.
I found a bench between the bookstore and the food court and sat there for a few minutes watching the world go by while I waited for the girls. It didn’t take me long to notice that teenage girls, especially the younger ones, seemed to be showing more leg now than I remembered. Short skirts that almost looked like what cheerleaders might wear seem to be a new trend. When a pair of slightly more mature cuties came by with a bit of butt cheek showing, I made a note to myself that I needed to get out more often.
A few minutes later, Cassie and Sally showed up, and we went to the food court. The nice thing about food courts is that everyone can get what they want, with no compromises. We sat at a table in the middle. I noticed both girls had bags from Victoria’s Secret, which, as their surrogate father for the day, I had to ask about.
“You don’t want to see mine,” Sally said, “it’s just undies.” She giggled and added, “Unless you’re into that.”
I tried to ignore that comment and quickly turned my attention to Cassie. “Should I ask what’s in your bag?”
“Not until we get home,” she said, sounding very mysterious.
“But you’ll like it,” Sally added.
That shook me a little. Cassie had bought something intimate that Sally thought I would like? It made me wonder just how many of our “secrets” my sometimes roommate was sharing with her friend.
“So, what’s in your bag?” Cassie asked.
I set it on the table and pulled out the chess book. I gave it to Sally. She looked at me and asked, “Just openings? Why not everything?”
“Because, young lady, a lot of the things I’ve been showing you are of no use if you start a game badly. So, take this and learn.”
“Can I bring it over next time I come for a lesson?”
“Sure, but don’t count on me to teach you everything. You can do some on your own.”
I gave Cassie the horse book. She smiled, then started leafing through it. When she finished, she looked at me and said, “This is great, Gary. So, when are we going riding again?”
“Maybe next weekend, if you’re free,” I said.
“Maybe Sally could go with us,” she said.
“Do I look like a horse person?” Sally asked.
“Just around the face,” Cassie said, and both girls laughed. I thought it was pretty funny too.
After that, we headed home because I had tutoring sessions to prepare for.
Friday evening was normal. Cassie and I got some leftovers from her home and reheated them. I had a session with one of the more annoying tutees I had to deal with, while Cass was playing video games on her laptop—just another quiet, ordinary evening. After I finished explaining quadratic equations to Stanley for the third time, I was worn out. Sometimes, just trying to keep your cool can do that. I was looking forward to some brainless TV, then a good night’s sleep, but there were a couple of things I needed to discuss with Cassie first. She was sitting on my sofa, so I sat down next to her. “Cass,” I asked, “what do you and Sally do when you go into your room and close the door? I hear a lot of giggling and laughing, so don’t tell me you’re doing homework.”
“Looking at stuff online, you know, TikTok, YouTube, goofy things people do.”
“But no porn?”
“What are you, my dad now?” she snapped, which confirmed my suspicions.
I had never seen her acting like this, so I knew I had hit a nerve. “That’s not an answer, Cassie, and yeah, when you spend as much time as you do with me, I kinda feel like your dad.”
“We’re not doing anything that most kids our age do. I bet you were looking at porn when you were fifteen.”
She had a valid point. I had started watching porn when I was thirteen. “We’re not talking about me now,” I snapped. “I don’t think it’s a good idea for girls like you and Sally to be watching adult videos.”
“What are you gonna do, ground me? Send me to my room?”
She had me there. I didn’t really have much leverage when it came to disciplining her. Besides, my heart wasn’t really in it anyway. The idea of my little sweetheart watching adults performing sex acts was, in a strange way, kind of exciting. I decided to give up that battle and move on to something more important.
“How much have you told Sally about what we do?” I ask, almost dreading the answer. “What did she mean, I’ll like what you bought at the mall today?”
“She was just being goofy,” Cassie told me, which wasn’t quite the comforting answer I was hoping for. “I’m careful. She kinda knows that we are more than just friends, but I know when to stop.”
“That’s good,” I told her. “You know how teenage girls are. Rumors, whether true or not, can spread like a California wildfire, and if the wrong person hears them, I could be in trouble.”
Cassie put her arm around my neck and told me, “I know I have to be very careful, Gary. I don’t want to lose what we have. Now, kiss me, or I’ll tell Sally what went on last night.”
“You little blackmailer,” I laughed, but it made me wonder if she would use that threat in the future. She hadn’t really needed to force me; I was more than willing to give her another kissing lesson. That led us to act like teenagers on a third date, with lots of hugging and touching. That was all right for Cassie, but I was no teenager. I had to get myself under control.
When things calmed down a bit, Cassie told me she was going to take a shower. I saw her coming out of her room carrying the box from Victoria’s Secret, so I knew she was going to show me what she had bought. I didn’t know if I was looking forward to that or was scared of what I might see.
She seemed to take longer than usual, which only made me more nervous. When she came out, she was wearing a ratty robe she often wore after her shower. She walked over to me with an evil grin on her face, stood a few feet in front of me, and asked, “Ready?”
I nodded, and she opened her robe, shrugged it off her shoulders, and let it drop to the floor. It looked like she had practiced that move. The nightgown she was wearing was about what I had expected. It was red, of course, and sheer enough that Cassie might as well have been nude. Something about seeing her small breasts and tiny nipples displayed like that made them even more desirable. The nightie itself ended at her waist, and below it were matching panties. I glanced down and saw her small patch of pubic hair, and just a shadow of her mons below it.
It could have been worse. She might have gone for one of those more extreme V.S. negligees, with cutouts for her breasts and a gap allowing easy access to her slit. Even though we had slept together and she had given me a hand job, I had never seen much of her body, but now - bam, there it was. And, like an idiot, the only thing I could say was, “How much did that cost?”
She ignored my inane question and asked, “Do you like it?”
“I like it a lot. Better not let your dad see it.”
That earned me a teenage eyeroll. “I’m not stupid. I’m going to keep it here.”
Then things got even more awkward. It looked like she was waiting for me to show more of a reaction, and I was trying hard not to. The temptation for me to gather her in my arms and carry her to my bed was becoming more than just a fantasy. After a few seconds of us staring at each other, Cassie made the next move in her obvious campaign to get me to do something I knew I had to resist.
She turned slowly, like a stripper displaying her wares. Her small tush, barely covered by the transparent material of the matching panties, was hard to ignore. I’ve always been a leg man, but a cute butt can still catch my attention. Mission accomplished, at least from Cassie’s point of view.
She turned again, facing me. Then she got on her knees in front of me, like she was begging, which, in a way, I guess was true. She put her hands on my thighs, then started moving them up my legs. When her fingers slid under my shorts, I was still trying to be cool, but when she found my hard dick, I knew whatever she wanted, she was going to get that night. Resistance, as the Star Trek meme goes, was futile.
“Fuck me, Gary,” she said, her voice so soft I hardly heard her.